From blues chords to bluegrass, Chris Thile takes listeners of his genre-bending quintet the Punch Brothers on as immersive an adventure as listeners of A Prairie Home Companion. “The question of genre becomes one of orchestration and texture,” Thile says of writing for and with his bandmates. “It’s content and intent, and you can put anything on any collection of instruments. A truly great piece of music, whether it’s by Radiohead or Bach [both of whom Punch Brothers have covered], survives any amount of orchestration. … We can get racy, no holds barred, anything’s on the table musically.” Their latest album, The Phosphorescent Blues, truly held nothing back, fusing “jazz instrumental chops and acoustic earthiness, Beach Boys harmonies and Debussy string dances, slinky acoustic rock songs and blues laments” (Chicago Tribune). Just before he took over as host of APHC last fall, Thile took another turn as a musical curator, leading a four-day festival of roots music at the Kennedy Center dubbed “American Acoustic.” This summer he takes the show on the road, stopping at Ravinia on August 14 along with I’m With Her, a folk trio comprising Thile’s Nickel Creek cofounder Sara Watkins along with Sarah Jarosz and Aoife O’Donovan, and jazz/folk guitarist Julian Lage.

But crossing genres is no simple thing, especially if it’s intended to be a permanent move. “You see a lot of people doing a one-off, saying, ‘This is my country record,’” Darius Rucker told Billboard in 2008, as he prepared for the release of his first post–Hootie & the Blowfish record. “[For] the people that say that they don’t get it, I’ll let the music speak for itself. I plan to do a lot of country records.” And that he has. Having since been inducted as a member of the Grand Ole Opry and become the third African American to win a country performance Grammy (for “Wagon Wheel”), Rucker is in the midst of work on his fifth country album, with one single, “If I Told You,” already released. “Rucker hits all the right notes and drops all the right references, but in country music, that’s not enough,” NPR observes. “Fans want … sincerity. Rucker is a rock star, but on his [albums], you hear the guy who still lives in and still loves his home state of South Carolina, right down to its sweet tea and kudzu.” Rucker returns to Ravinia on August 5 with Radney Foster, whose hit solo debut—following making a handful of top-10 singles as half of Foster & Lloyd, including “Crazy Over You” and “Fair Shake”—the autobiographically titled Del Rio, TX 1959, inspired the title of Rucker’s second country album.

Four years ago, Sheryl Crow crossed over from “that rare balance between retro, organic rock and slick glam-pop” (Slant) that made her a radio darling through the late ’90s and the first decade of the 21st century into the grassy world of country with Feels Like Home, on which Rolling Stone said she “makes every twang her own … [serving] a half-century’s worth of styles without sounding like a history teacher.” On her newest record, Be Myself, Crow winds her way back toward her own musical roots, enlisting the producers from her second and third albums, 1996’s Sheryl Crow (“Home,” “A Change Would Do You Good,” “If It Makes You Happy”) and 1998’s The Globe Sessions (“There Goes the Neighborhood,” “Anything But Down”). “I wanted to revisit that sound and that feeling,” she told Billboard of uniting those early days with the present. “It was a complete blast, and the most effortless thing I’ve ever done.” She will bring the sounds of her self-rediscovery to Ravinia on July 7, an evening that will be opened by Lukas Nelson & Promise of the Real, playing what they dub their signature “cowboy hippie surf rock.”

Three weeks earlier, on June 16, Lukas will also be opening for his legendary father, Willie Nelson, as the family band reassembles at Ravinia for an evening of the Red-Headed Stranger’s unimpeachable hits, a catalogue the Pittsburgh Post-Gazette calls “the jukebox from the roadhouse in some honky-tonk heaven.” Even in his 80s, the paper also says, he is “still near the height of his powers, with a national treasure of a voice aged like a top-shelf whiskey.”